Reference of 112110-07-3, Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps,and cheap raw materials. 112110-07-3, name is 5-(Trifluoromethyl)pyridin-3-amine. A new synthetic method of this compound is introduced below.
To degassed dioxane (10mL) were added sequentially 5- trifluoromethylpyridin-3-amine (2) (309mg, 1.9mmol), 2-chloropyrazine (1) (0.26mL, 2.86mmol), Pd2(dba)3 (52mg, 0.06mmol), XantPhos (66mg, 0.1 1 mmol) and Cs2C03 (1.24g, 3.8mmol) with continued degassing. The reaction mixture was heated up to 90C overnight. An additional portion of 2-chloropyrazine (0.17ml_, 1.91 mmol) was then added and the reaction mixture was heated up to (0304) 90C overnight. Once cooled down to rt, it was poured into H20 (20ml_) and extracted with EtOAc (3 x 20ml_). The combined organic extracts were dried over MgS04, filtered and concentrated in vacuo. Purification by silica gel column chromatography with hexane/EtOAc (1 :0-1 :2) gave a residue which was re- dissolved in CH2CI2/MeOH (4:1 , 50ml_) and swirled with MP-TMT resin (440mg, 1.3mmol/g) at rt overnight. The solution was filtered, the resin washed with CH2CI2/MeOH (4:1 , 100ml_) and the filtrate concentrated in vacuo to yield (3) as a yellow solid (202mg, 44%). (0305) LCMS (ES): Found 241.0 [M+Hf. (0306) 1H NMR (300 MHz, DMSO-cf6), d: 10.14 (s, 1 H), 9.00 (d, J=2.4 Hz, 1 H), 8.69 (t, J= 2.0 Hz, 1 H), 8.52 (d, J=0.9 Hz, 1 H), 8.32 (d, J=1.5 Hz, 1 H), 8.25 (dd, J= 2.8, 1.5 Hz, 1 H), 8.08 (d, J= 2.8 Hz, 1 H). (0307) 19F NMR (282 MHz, DMSO-cf6), d: -61.09 (s, 3F).
At the same time, in my other blogs, there are other synthetic methods of this type of compound,112110-07-3, 5-(Trifluoromethyl)pyridin-3-amine, and friends who are interested can also refer to it.
Reference:
Patent; KARUS THERAPEUTICS LIMITED; SHUTTLEWORTH, Stephen Joseph; GATLAND, Alice Elizabeth; FINNEMORE, Daniel John; ALEXANDER, Rikki Peter; SILVA, Franck; CECIL, Alexander; (233 pag.)WO2019/166824; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem